CN1169801C - 由烯烃制备环氧化物的方法 - Google Patents
由烯烃制备环氧化物的方法 Download PDFInfo
- Publication number
- CN1169801C CN1169801C CNB001243152A CN00124315A CN1169801C CN 1169801 C CN1169801 C CN 1169801C CN B001243152 A CNB001243152 A CN B001243152A CN 00124315 A CN00124315 A CN 00124315A CN 1169801 C CN1169801 C CN 1169801C
- Authority
- CN
- China
- Prior art keywords
- hydrogen peroxide
- alkali
- value
- epoxidation
- propylene
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 150000002118 epoxides Chemical class 0.000 title abstract 2
- 238000004519 manufacturing process Methods 0.000 title description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims abstract description 133
- 238000000034 method Methods 0.000 claims abstract description 35
- 238000006735 epoxidation reaction Methods 0.000 claims abstract description 29
- 239000000203 mixture Substances 0.000 claims abstract description 27
- 150000001875 compounds Chemical class 0.000 claims abstract description 7
- 238000002360 preparation method Methods 0.000 claims abstract description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical group OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 41
- 239000003513 alkali Substances 0.000 claims description 31
- 150000001336 alkenes Chemical class 0.000 claims description 25
- 238000006243 chemical reaction Methods 0.000 claims description 23
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 22
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 claims description 17
- GNKTZDSRQHMHLZ-UHFFFAOYSA-N [Si].[Si].[Si].[Ti].[Ti].[Ti].[Ti].[Ti] Chemical compound [Si].[Si].[Si].[Ti].[Ti].[Ti].[Ti].[Ti] GNKTZDSRQHMHLZ-UHFFFAOYSA-N 0.000 claims description 15
- 239000002904 solvent Substances 0.000 claims description 14
- 239000011521 glass Substances 0.000 claims description 12
- 229910021529 ammonia Inorganic materials 0.000 claims description 11
- 239000007789 gas Substances 0.000 claims description 11
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims description 11
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 11
- 239000007864 aqueous solution Substances 0.000 claims description 10
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims description 10
- 239000002994 raw material Substances 0.000 claims description 10
- 229920001296 polysiloxane Polymers 0.000 claims description 9
- 239000000243 solution Substances 0.000 claims description 9
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 7
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 7
- 229910052783 alkali metal Inorganic materials 0.000 claims description 6
- 239000003960 organic solvent Substances 0.000 claims description 6
- -1 alkali metal carboxylate Chemical class 0.000 claims description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 4
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims description 3
- 150000001340 alkali metals Chemical class 0.000 claims description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 2
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 claims description 2
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 claims description 2
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 claims description 2
- UXFQFBNBSPQBJW-UHFFFAOYSA-N 2-amino-2-methylpropane-1,3-diol Chemical compound OCC(N)(C)CO UXFQFBNBSPQBJW-UHFFFAOYSA-N 0.000 claims description 2
- POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 claims description 2
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 claims description 2
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 claims description 2
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims description 2
- KZDCMKVLEYCGQX-UDPGNSCCSA-N 2-(diethylamino)ethyl 4-aminobenzoate;(2s,5r,6r)-3,3-dimethyl-7-oxo-6-[(2-phenylacetyl)amino]-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid;hydrate Chemical class O.CCN(CC)CCOC(=O)C1=CC=C(N)C=C1.N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=CC=C1 KZDCMKVLEYCGQX-UDPGNSCCSA-N 0.000 claims 2
- 229910000318 alkali metal phosphate Inorganic materials 0.000 claims 1
- 239000011541 reaction mixture Substances 0.000 abstract description 14
- 239000003054 catalyst Substances 0.000 abstract description 12
- 230000008569 process Effects 0.000 abstract description 5
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 abstract description 3
- 239000000126 substance Substances 0.000 abstract description 3
- 239000010936 titanium Substances 0.000 abstract description 3
- 229910052719 titanium Inorganic materials 0.000 abstract description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 21
- 230000009466 transformation Effects 0.000 description 15
- 238000005259 measurement Methods 0.000 description 12
- 239000003795 chemical substances by application Substances 0.000 description 9
- 230000003472 neutralizing effect Effects 0.000 description 9
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 8
- 150000002924 oxiranes Chemical class 0.000 description 8
- 230000000694 effects Effects 0.000 description 7
- 229910021607 Silver chloride Inorganic materials 0.000 description 6
- 230000003197 catalytic effect Effects 0.000 description 6
- HKZLPVFGJNLROG-UHFFFAOYSA-M silver monochloride Chemical compound [Cl-].[Ag+] HKZLPVFGJNLROG-UHFFFAOYSA-M 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 239000002253 acid Substances 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 4
- 230000002950 deficient Effects 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 239000011230 binding agent Substances 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 238000004817 gas chromatography Methods 0.000 description 3
- 230000001590 oxidative effect Effects 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- 238000004448 titration Methods 0.000 description 3
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 2
- 229910021536 Zeolite Inorganic materials 0.000 description 2
- XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 description 2
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 description 2
- 150000004056 anthraquinones Chemical class 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 229910052728 basic metal Inorganic materials 0.000 description 2
- 150000003818 basic metals Chemical class 0.000 description 2
- 229910021538 borax Inorganic materials 0.000 description 2
- 238000006555 catalytic reaction Methods 0.000 description 2
- 230000008859 change Effects 0.000 description 2
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000007142 ring opening reaction Methods 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- VWDWKYIASSYTQR-UHFFFAOYSA-N sodium nitrate Chemical compound [Na+].[O-][N+]([O-])=O VWDWKYIASSYTQR-UHFFFAOYSA-N 0.000 description 2
- 239000004328 sodium tetraborate Substances 0.000 description 2
- 235000010339 sodium tetraborate Nutrition 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- 239000010457 zeolite Substances 0.000 description 2
- LHENQXAPVKABON-UHFFFAOYSA-N 1-methoxypropan-1-ol Chemical compound CCC(O)OC LHENQXAPVKABON-UHFFFAOYSA-N 0.000 description 1
- OSDWBNJEKMUWAV-UHFFFAOYSA-N Allyl chloride Chemical group ClCC=C OSDWBNJEKMUWAV-UHFFFAOYSA-N 0.000 description 1
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 229910004298 SiO 2 Inorganic materials 0.000 description 1
- 229910010413 TiO 2 Inorganic materials 0.000 description 1
- 238000007171 acid catalysis Methods 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 235000012538 ammonium bicarbonate Nutrition 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 230000005587 bubbling Effects 0.000 description 1
- 238000004364 calculation method Methods 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 150000004292 cyclic ethers Chemical class 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 229910001882 dioxygen Inorganic materials 0.000 description 1
- XPPKVPWEQAFLFU-UHFFFAOYSA-J diphosphate(4-) Chemical class [O-]P([O-])(=O)OP([O-])([O-])=O XPPKVPWEQAFLFU-UHFFFAOYSA-J 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- GPRLSGONYQIRFK-UHFFFAOYSA-N hydron Chemical compound [H+] GPRLSGONYQIRFK-UHFFFAOYSA-N 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 238000013383 initial experiment Methods 0.000 description 1
- 238000005304 joining Methods 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 238000000691 measurement method Methods 0.000 description 1
- 238000012544 monitoring process Methods 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 238000001139 pH measurement Methods 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 150000003016 phosphoric acids Chemical class 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 235000010344 sodium nitrate Nutrition 0.000 description 1
- 239000004317 sodium nitrate Substances 0.000 description 1
- 229940001516 sodium nitrate Drugs 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D301/00—Preparation of oxiranes
- C07D301/02—Synthesis of the oxirane ring
- C07D301/03—Synthesis of the oxirane ring by oxidation of unsaturated compounds, or of mixtures of unsaturated and saturated compounds
- C07D301/12—Synthesis of the oxirane ring by oxidation of unsaturated compounds, or of mixtures of unsaturated and saturated compounds with hydrogen peroxide or inorganic peroxides or peracids
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Inorganic Chemistry (AREA)
- Epoxy Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Catalysts (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19944839.6 | 1999-09-18 | ||
| DE19944839A DE19944839A1 (de) | 1999-09-18 | 1999-09-18 | Verfahren zur Herstellung von Epoxiden aus Olefinen |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN1288889A CN1288889A (zh) | 2001-03-28 |
| CN1169801C true CN1169801C (zh) | 2004-10-06 |
Family
ID=7922523
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CNB001243152A Expired - Lifetime CN1169801C (zh) | 1999-09-18 | 2000-09-01 | 由烯烃制备环氧化物的方法 |
Country Status (21)
| Country | Link |
|---|---|
| US (1) | US6372924B2 (es) |
| EP (1) | EP1085017B1 (es) |
| JP (1) | JP2001097966A (es) |
| KR (1) | KR20010039887A (es) |
| CN (1) | CN1169801C (es) |
| AR (1) | AR025639A1 (es) |
| AT (1) | ATE295359T1 (es) |
| AU (1) | AU5941600A (es) |
| BR (1) | BR0004223A (es) |
| CA (1) | CA2319284A1 (es) |
| DE (2) | DE19944839A1 (es) |
| ES (1) | ES2239569T3 (es) |
| ID (1) | ID27314A (es) |
| IL (1) | IL138495A0 (es) |
| MX (1) | MXPA00008930A (es) |
| NO (1) | NO20004606L (es) |
| NZ (1) | NZ506789A (es) |
| PL (1) | PL342594A1 (es) |
| RU (1) | RU2000123668A (es) |
| SG (1) | SG91883A1 (es) |
| TR (1) | TR200002230A3 (es) |
Families Citing this family (52)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1122247A1 (de) | 2000-02-07 | 2001-08-08 | Degussa AG | Verfahren zur Epoxidierung von Olefinen |
| EP1122248A1 (de) | 2000-02-07 | 2001-08-08 | Degussa AG | Verfahren zur Epoxidierung von Olefinen |
| EP1122246A1 (de) | 2000-02-07 | 2001-08-08 | Degussa AG | Verfahren zur Epoxidierung von Olefinen |
| ES2349004T3 (es) | 2001-01-08 | 2010-12-21 | Evonik Degussa Gmbh | Procedimiento para la epoxidacion de olefinas. |
| US6608219B2 (en) | 2001-06-13 | 2003-08-19 | Degussa Ag | Process for the epoxidation of olefins |
| US6600055B2 (en) | 2001-06-13 | 2003-07-29 | Degussa Ag | Process for the epoxidation of olefins |
| US6596881B2 (en) | 2001-06-13 | 2003-07-22 | Degussa Ag | Process for the epoxidation of olefins |
| US6749668B2 (en) * | 2001-06-18 | 2004-06-15 | Degussa Ag | Process for the recovery of combustible components of a gas stream |
| US6610865B2 (en) | 2001-08-15 | 2003-08-26 | Degussa Ag | Process for the epoxidation of olefins |
| US6596883B2 (en) | 2001-08-23 | 2003-07-22 | Degussa Ag | Process for the epoxidation of olefins |
| US6498259B1 (en) † | 2001-10-19 | 2002-12-24 | Arco Chemical Technology L.P. | Direct epoxidation process using a mixed catalyst system |
| US6720436B2 (en) * | 2002-03-18 | 2004-04-13 | Degussa Ag | Process for the epoxidation of olefins |
| EP1346986A1 (en) * | 2002-03-18 | 2003-09-24 | Degussa AG | Process for the epoxidation of olefins |
| US7141683B2 (en) * | 2002-05-02 | 2006-11-28 | Degussa Ag | Process for the epoxidation of olefins |
| US20040000473A1 (en) * | 2002-06-20 | 2004-01-01 | Willi Hofen | Process of separating 1-methoxy-2-propanol and 2-methoxy-1-propanol from aqueous compositions |
| US7722847B2 (en) * | 2002-09-30 | 2010-05-25 | Evonik Degussa Gmbh | Aqueous hydrogen peroxide solutions and method of making same |
| US6838572B2 (en) * | 2002-09-30 | 2005-01-04 | Degussa Ag | Process for the epoxidation of olefins |
| EP1403259A1 (en) * | 2002-09-30 | 2004-03-31 | Degussa AG | Process for the epoxidation of olefins |
| FR2846965B1 (fr) * | 2002-11-12 | 2006-10-13 | Procede de fabrication de 1,2-epoxy-3-chloropropane | |
| FR2846964B1 (fr) * | 2002-11-12 | 2006-07-21 | Procede de fabrication de 1,2-epoxy-3-chloropropane | |
| US7169945B2 (en) * | 2002-11-26 | 2007-01-30 | Degussa Ag | Process for the epoxidation of olefins |
| EP1424331A1 (en) * | 2002-11-26 | 2004-06-02 | Degussa AG | Process for the epoxidation of olefins |
| KR101131207B1 (ko) * | 2004-03-31 | 2012-03-28 | 카운슬 오브 사이언티픽 앤드 인더스트리얼 리서치 | 알켄으로부터 에폭시드를 제조하기 위한 개선된 촉매 방법 |
| KR101166932B1 (ko) * | 2005-07-27 | 2012-07-19 | 에스케이이노베이션 주식회사 | 티타늄 함유 분자체 촉매의 재생방법 |
| KR101363833B1 (ko) * | 2005-12-27 | 2014-02-14 | 바스프 에스이 | 프로펜의 에폭시화 방법 |
| JP4820663B2 (ja) * | 2006-02-22 | 2011-11-24 | パナソニック環境エンジニアリング株式会社 | 過酸化水素含有廃液の処理方法及び処理装置 |
| EP2035402B1 (en) * | 2006-06-23 | 2018-11-21 | Blue Cube IP LLC | Process for producing epoxides from olefinic compounds |
| US8558020B2 (en) * | 2007-04-05 | 2013-10-15 | Solvay (Societe Anonyme) | Aqueous hydrogen peroxide solution, process for its preparation and use thereof |
| WO2009129355A1 (en) * | 2008-04-18 | 2009-10-22 | Dow Global Technologies Inc. | Integrated process for the production of chlorinated epoxides such as epichlorohydrin |
| US20120130096A1 (en) * | 2009-08-05 | 2012-05-24 | Crampton Hannah L | Process for producing propylene oxide |
| US20120226056A1 (en) * | 2009-11-19 | 2012-09-06 | Crampton Hannah L | Epoxidizing propylene |
| WO2011062608A2 (en) * | 2009-11-19 | 2011-05-26 | Dow Global Technologies, Inc. | Epoxidation of an olefin |
| EP2343288A1 (en) | 2009-11-27 | 2011-07-13 | Momentive Specialty Chemicals Research Belgium S.A. | Process for the manufacture of propylene oxide |
| EP2354131A1 (en) | 2010-02-02 | 2011-08-10 | Momentive Specialty Chemicals Research Belgium | Process for the manufacture of a 1,2-epoxide and a device for carrying out said process |
| MY157638A (en) | 2010-12-07 | 2016-07-15 | Basf Se | Process for the production of propylene oxide |
| US8785670B2 (en) | 2010-12-07 | 2014-07-22 | Basf Se | Process for the production of propylene oxide |
| US11731118B2 (en) * | 2012-10-10 | 2023-08-22 | Albemarle Catalysts Company B.V. | Supported hydrotreating catalysts having enhanced activity |
| ES2767100T3 (es) | 2014-07-29 | 2020-06-16 | Evonik Operations Gmbh | Procedimiento para la epoxidación de una olefina |
| JP6681007B2 (ja) * | 2014-08-20 | 2020-04-15 | 日産化学株式会社 | 過酸化水素の安定化剤を含有するエポキシ化合物の製造方法 |
| EP3059229A1 (en) | 2015-02-17 | 2016-08-24 | Evonik Degussa GmbH | Method for the epoxidation of an olefin with hydrogen peroxide |
| TW201700464A (zh) * | 2015-02-17 | 2017-01-01 | 贏創德固賽有限責任公司 | 使用過氧化氫之使烯烴環氧化方法 |
| CN107257792B (zh) | 2015-02-17 | 2021-04-02 | 赢创运营有限公司 | 用过氧化氢环氧化烯烃的方法 |
| PL3288927T3 (pl) | 2015-04-28 | 2020-03-31 | Evonik Degussa Gmbh | Sposób epoksydacji propenu |
| EP3380448B1 (de) | 2015-11-25 | 2019-08-28 | Evonik Degussa GmbH | Verfahren zur herstellung von 1,2-propandiol aus propen und wasserstoffperoxid |
| WO2017089074A1 (en) | 2015-11-26 | 2017-06-01 | Evonik Degussa Gmbh | Process for the epoxidation of an olefin |
| TWI707847B (zh) | 2015-11-26 | 2020-10-21 | 德商贏創運營有限公司 | 丙烯之環氧化方法 |
| HUE054720T2 (hu) | 2015-11-26 | 2021-09-28 | Evonik Operations Gmbh | Eljárás és reaktor propén epoxidálására |
| US10676450B2 (en) | 2016-01-19 | 2020-06-09 | Evonik Operations Gmbh | Process for the epoxidation of an olefin |
| MY185641A (en) | 2016-03-21 | 2021-05-27 | Evonik Operations Gmbh | Process for the epoxidation of propene |
| EP3246323A1 (en) | 2016-05-17 | 2017-11-22 | Evonik Degussa GmbH | Integrated process for making propene oxide from propane |
| EP3406603A1 (en) | 2017-05-22 | 2018-11-28 | Evonik Degussa GmbH | Process for the epoxidation of propene |
| CN110256376B (zh) * | 2019-06-14 | 2022-07-19 | 大连理工大学 | 一种丙烯和过氧化氢气相环氧化合成环氧丙烷的流态化反应方法 |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT1152296B (it) | 1982-07-28 | 1986-12-31 | Anic Spa | Procedimento per la sintesi di monometileteri dei glicoli |
| ES2033693T3 (es) | 1986-01-28 | 1993-04-01 | Eniricerche S.P.A. | Un procedimiento para la exposidacion de compuestos olefinicos. |
| US5412122A (en) * | 1993-12-23 | 1995-05-02 | Arco Chemical Technology, L.P. | Epoxidation process |
| IT1283232B1 (it) * | 1996-03-12 | 1998-04-16 | Enichem Spa | Procedimento per la sintesi di 2-buten-1, 4-diesteri |
| US5912367A (en) * | 1997-07-01 | 1999-06-15 | Arco Chemical Technology, L.P. | High efficiency epoxidation process |
| BE1011851A3 (fr) * | 1998-03-24 | 2000-02-01 | Solvay | Procede de fabrication d'un oxiranne. |
-
1999
- 1999-09-18 DE DE19944839A patent/DE19944839A1/de not_active Ceased
-
2000
- 2000-08-30 ES ES00118709T patent/ES2239569T3/es not_active Expired - Lifetime
- 2000-08-30 EP EP00118709A patent/EP1085017B1/de not_active Expired - Lifetime
- 2000-08-30 AT AT00118709T patent/ATE295359T1/de not_active IP Right Cessation
- 2000-08-30 DE DE50010273T patent/DE50010273D1/de not_active Expired - Lifetime
- 2000-09-01 CN CNB001243152A patent/CN1169801C/zh not_active Expired - Lifetime
- 2000-09-06 NZ NZ506789A patent/NZ506789A/en unknown
- 2000-09-12 AR ARP000104780A patent/AR025639A1/es unknown
- 2000-09-12 MX MXPA00008930A patent/MXPA00008930A/es unknown
- 2000-09-13 AU AU59416/00A patent/AU5941600A/en not_active Abandoned
- 2000-09-14 CA CA002319284A patent/CA2319284A1/en not_active Abandoned
- 2000-09-15 BR BR0004223-4A patent/BR0004223A/pt not_active IP Right Cessation
- 2000-09-15 TR TR2000/02230A patent/TR200002230A3/tr unknown
- 2000-09-15 KR KR1020000054164A patent/KR20010039887A/ko not_active Application Discontinuation
- 2000-09-15 NO NO20004606A patent/NO20004606L/no unknown
- 2000-09-15 IL IL13849500A patent/IL138495A0/xx active IP Right Grant
- 2000-09-15 ID IDP20000798A patent/ID27314A/id unknown
- 2000-09-15 SG SG200005266A patent/SG91883A1/en unknown
- 2000-09-18 JP JP2000282596A patent/JP2001097966A/ja active Pending
- 2000-09-18 RU RU2000123668/04A patent/RU2000123668A/ru not_active Application Discontinuation
- 2000-09-18 US US09/663,703 patent/US6372924B2/en not_active Expired - Lifetime
- 2000-09-18 PL PL00342594A patent/PL342594A1/xx not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| IL138495A0 (en) | 2001-10-31 |
| KR20010039887A (ko) | 2001-05-15 |
| NO20004606D0 (no) | 2000-09-15 |
| EP1085017B1 (de) | 2005-05-11 |
| CA2319284A1 (en) | 2001-03-18 |
| US6372924B2 (en) | 2002-04-16 |
| DE19944839A1 (de) | 2001-03-22 |
| AU5941600A (en) | 2001-03-22 |
| SG91883A1 (en) | 2002-10-15 |
| EP1085017A1 (de) | 2001-03-21 |
| DE50010273D1 (de) | 2005-06-16 |
| TR200002230A2 (tr) | 2001-04-20 |
| TR200002230A3 (tr) | 2001-04-20 |
| ES2239569T3 (es) | 2005-10-01 |
| ATE295359T1 (de) | 2005-05-15 |
| US20020004606A1 (en) | 2002-01-10 |
| NZ506789A (en) | 2002-03-01 |
| JP2001097966A (ja) | 2001-04-10 |
| ID27314A (id) | 2001-03-22 |
| MXPA00008930A (es) | 2005-07-15 |
| BR0004223A (pt) | 2001-04-10 |
| PL342594A1 (en) | 2001-03-26 |
| RU2000123668A (ru) | 2002-08-10 |
| AR025639A1 (es) | 2002-12-04 |
| CN1288889A (zh) | 2001-03-28 |
| NO20004606L (no) | 2001-03-19 |
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